$165 Find Cheap Flights from Hawaii to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$360
Overall average: $746
United Airlines
Thu 4/30Wed 5/6
HNL - ORD • 1 stop
Cheapest non-stop
$492
Typical prices: $842-$1,043
American Airlines
Sun 3/29Sun 4/12
HNL - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Hawaii to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hawaii to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hawaii to Chicago

Thu, Apr 30 - Wed, May 6
United Airlines Logo
7:00 am - 11:28 pm
HNL
-
ORD
11h 28m
1 stop
United Airlines Logo
1:43 pm - 8:09 pm
ORD
-
HNL
11h 26m
1 stop
$360United Airlines
Wed, Apr 15 - Mon, Apr 20
Multiple Airlines Logo
7:50 am - 5:50 am
HNL
-
ORD
17h 00m
1 stop
Multiple Airlines Logo
9:14 pm - 9:59 am
ORD
-
HNL
17h 45m
1 stop
$376Multiple Airlines
Fri, Apr 17 - Wed, Apr 29
Alaska Airlines Logo
11:02 pm - 7:02 pm
OGG
-
ORD
15h 00m
1 stop
Alaska Airlines Logo
8:50 am - 8:52 pm
ORD
-
OGG
17h 02m
1 stop
$402Alaska Airlines
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
8:10 am - 4:35 am
HNL
-
MDW
15h 25m
1 stop
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
$411Southwest
Wed, Apr 22 - Wed, Apr 29
Alaska Airlines Logo
10:51 pm - 11:43 pm
OGG
-
ORD
19h 52m
1 stop
Alaska Airlines Logo
8:50 am - 8:52 pm
ORD
-
OGG
17h 02m
1 stop
$412Alaska Airlines
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
11:50 am - 5:55 am
HNL
-
MDW
13h 05m
1 stop
Southwest Logo
10:05 am - 9:00 pm
MDW
-
HNL
15h 55m
1 stop
$416Southwest
Tue, Apr 21 - Tue, Apr 28
Delta Logo
9:15 pm - 4:39 pm
OGG
-
ORD
14h 24m
1 stop
Delta Logo
7:15 am - 5:36 pm
ORD
-
OGG
15h 21m
1 stop
$422Delta
Thu, Apr 23 - Tue, May 5
Delta Logo
8:50 pm - 1:23 pm
KOA
-
ORD
11h 33m
1 stop
Delta Logo
7:15 am - 7:03 pm
ORD
-
KOA
16h 48m
1 stop
$424Delta
Mon, Apr 20 - Mon, Apr 27
American Airlines Logo
9:45 pm - 2:16 pm
OGG
-
ORD
11h 31m
1 stop
American Airlines Logo
6:00 am - 1:24 pm
ORD
-
OGG
12h 24m
1 stop
$425American Airlines
Tue, Apr 7 - Sun, Apr 12
American Airlines Logo
1:22 pm - 5:47 am
KOA
-
ORD
11h 25m
1 stop
American Airlines Logo
7:04 am - 2:26 pm
ORD
-
KOA
12h 22m
1 stop
$501American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$165
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 41% increase in price.
Flight from Kailua-Kona to Chicago O'Hare Airport

FAQs for booking flights from Hawaii to Chicago

  • How does KAYAK find such low prices on flights from Hawaii to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hawaii to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $2,717
Business Class flights to Chicagofrom $2,872
Premium Economy Class flights to Chicagofrom $694
Economy Class flights to Chicagofrom $334